Molecular design and an attempt to synthesize a conjugate of 2-methoxyestradiol with adamantane

Based on molecular modeling data, 2-adamantyl 8-[(2-methoxyestra-1,3,5(10)-triene-3,17β-diol-6α-yl)amino]octanoate 2d is proposed as a structural analogue of highly cytotoxic N -(8-(adamant-2-yloxi)-8-oxooctanoyl)- N -deacetylcolchycine. Three-step synthesis of adamant-2-yl 8-aminooctanoate 5 is des...

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Bibliographic Details
Published in:Moscow University chemistry bulletin 2015-03, Vol.70 (2), p.69-73
Main Authors: Zefirov, N. A., Glazkova, Ya. S., Kuznetsova, I. V., Nurieva, E. V., Zefirova, O. N.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
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Summary:Based on molecular modeling data, 2-adamantyl 8-[(2-methoxyestra-1,3,5(10)-triene-3,17β-diol-6α-yl)amino]octanoate 2d is proposed as a structural analogue of highly cytotoxic N -(8-(adamant-2-yloxi)-8-oxooctanoyl)- N -deacetylcolchycine. Three-step synthesis of adamant-2-yl 8-aminooctanoate 5 is described. Reductive amination of 2-methoxy-6-oxo-17β-estradiol in weakly acidic medium in the presence of compound 5 and NaBH 3 CN or Na(OAc) 3 BH results in the product of elimination at the C 6 –C 7 bond of steroid 7 rather than the formation of conjugate 2d .
ISSN:0027-1314
1935-0260
DOI:10.3103/S0027131415020108